ID: ALA1200468

Max Phase: Approved

First Approval: 1982

Molecular Formula: C10H19O6PS2

Molecular Weight: 330.36

Molecule Type: Small molecule

Representations

Synonyms (6): Malathion | 8059HC | ENT 17,034 | ENT-17034 | NSC-6524 | OVIDE
Synonyms from Alternative Forms(6):

Trade Names(8): Cythion | Derbac-m | Malathion | Organoderm | Ovide | Prioderm | Quellada-m | Suleo-m

Canonical SMILES:  CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC

Standard InChI:  InChI=1S/C10H19O6PS2/c1-5-15-9(11)7-8(10(12)16-6-2)19-17(18,13-3)14-4/h8H,5-7H2,1-4H3

Standard InChI Key:  JXSJBGJIGXNWCI-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: No

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 330.36

Molecular Weight (Monoisotopic): 330.0361

AlogP: 2.12

#Rotatable Bonds: 9

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 8

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 1.86

CX LogD: 1.86

Aromatic Rings: 0

Heavy Atoms: 19

QED Weighted: 0.47

Np Likeness Score: -0.04

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

3. Fourches D, Barnes JC, Day NC, Bradley P, Reed JZ, Tropsha A..  (2010)  Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.,  23  (1): [PMID:20014752] [10.1021/tx900326k]

4. Unpublished dataset, 

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

8. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

9. Aggarwal N, Kumar R, Srivastva C, Dureja P, Khurana JM..  (2010)  Synthesis of nalidixic acid based hydrazones as novel pesticides.,  58  (5): [PMID:20131903] [10.1021/jf904144e]

10. Ahmad NW, Huang TS, Balabaskaran S, Lo KM, Das VG..  (1994)  Insecticidal Effects of Organotin(IV) Compounds on Plutella Xylostella (L.) Larvae. II. Inhibitory Potencies Against Acetylcholinesterase and Evidence for Synergism in Tests With Bacillus Thuringiensis(BER.) and Malathion.,  1  (1): [PMID:18476213] [10.1155/mbd.1994.1]

11. Ujváry I, Matolcsy G, Bélai I, Szurdoki F, Bauer K, Varjas L, Kramer KJ..  (1996)  Projuvenoids: synthesis and biological evaluation of sulfenylated, sulfinylated, and sulfonylated carbamates.,  32  (3): [PMID:8756313] [10.1002/(sici)1520-6327(1996)32:3/4<659::aid-arch37>3.3.co;2-w]

12. Yoshikawa H, Ueno R.  (1992)  Synthesis and Insecticidal Activity of 2-Alkoxy-4H-l,3,2-benzoxazaphosphorin-2-thiones,  56  (9): [10.1271/bbb.56.1467]

13. YOSHIKAWA H.  (2000)  Synthesis and Insecticidal Activity of O-Aryl N-Alkoxycarbonyl-N-alkylmethylphosphonamidothionates,  25  (4): [10.1584/jpestics.25.392]

14. Macedo PEF, Maffia LA, Cota LV, Louren^|^ccedil;o V, Mizubuti ESG.  (2012)  Sensitivity of four isolates of Clonostachys rosea to pesticides used in the strawberry crop in Brazil,  37  (4): [10.1584/jpestics.D11-055]

15. Yokoyama A, Ohtsu K, Iwafune T, Nagai T, Ishihara S, Kobara Y, Horio T, Endo S.  (2009)  A useful new insecticide bioassay using first-instar larvae of a net-spinning caddisfly, Cheumatopsyche brevilineata (Trichoptera: Hydropsychidae),  34  (1): [10.1584/jpestics.G08-26]

16. ENDO S, TSURUMACHI M.  (2000)  Insecticide Resistance and Insensitive Acetylcholinesterase in Small Brown Planthopper, Laodelphax striatellus,  25  (4): [10.1584/jpestics.25.395]

17. Bruck DJ, Bolda M, Tanigoshi L, Klick J, Kleiber J, DeFrancesco J, Gerdeman B, Spitler H..  (2011)  Laboratory and field comparisons of insecticides to reduce infestation of Drosophila suzukii in berry crops.,  67  (11): [PMID:21800409] [10.1002/ps.2242]

18. Chandak N, Bhardwaj JK, Sharma RK, Sharma PK..  (2013)  Inhibitors of apoptosis in testicular germ cells: synthesis and biological evaluation of some novel IBTs bearing sulfonamide moiety.,  59  [PMID:23220649] [10.1016/j.ejmech.2012.11.015]

19. PubChem BioAssay data set, 

20. Unpublished dataset, 

21. PubChem BioAssay data set, 

22. Castelino PA, Naik P, Dasappa JP, Sujayraj RS, Sharath Chandra K, Chaluvaiah K, Nair R, Sandya Kumari MV, Kalthur G, Adiga SK..  (2014)  Synthesis of novel thiadiazolotriazin-4-ones and study of their mosquito-larvicidal and antibacterial properties.,  84  [PMID:25019476] [10.1016/j.ejmech.2014.06.072]

23. WHO Anatomical Therapeutic Chemical Classification, 

24. British National Formulary (72nd edition), 

25. Unpublished dataset, 

26. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

27. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(9):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• Gene Expression Atlas Compounds
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• IMI-CARE SARS-CoV-2 Data